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“In the future, there will be no female leaders. There will just be leaders.” 
― Sheryl Sandberg

I Worked Two Jobs to Fund My Dream Career. Here’s Why I’d Do It Again.

I Worked Two Jobs to Fund My Dream Career. Here’s Why I’d Do It Again.

Written by Mandy Shold // Edited by Chelsea DuDeVoire

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Directly following my college graduation, I scored the job of my dreams and shortly began working my way up in the company. Paired with my perfect little apartment adorned with black-and-white checkered floors, I began living the San Francisco life that I had always hoped for. 

In-between spending my days at the office and retreating home to my darling apartment, though, was another obligation – my part-time job.

The dream life I was living wasn’t solely being funded by my entry-level full-time job in the most expensive city in the United States. I achieved this dream by working as a barista on nights and weekends, and after nearly three years of fueling other people’s caffeine addictions in the moments where I needed sleep more than anything, I finally hung up my apron for good this month.

Did I breathe a sigh of relief? Hell yes. Would I do it again? You bet.

Here’s why.


I’ve always known what I wanted to do. For me, it wasn’t so much a career as it was a calling. And I didn’t care – eh, tried not to care – whether or not I made much money in the process. I’ve also always known that I wanted to spend my twenties in a big city – preferably one with Instagram-worthy photo ops, bridges and cable car commutes.

And finally, I knew I wanted to live alone. An impractical, damn near impossible, dream in San Francisco, unless, of course, your startup panned into success or you work for the likes of Facebook or Google. Or, perhaps, unless you work more than one job.

Enter my glamorous job as a barista, also known as the side job that financed my full-time hustle. By day it was high heels and email etiquette – and by night it was hair ties and latte art. But for me, working nights and weekends wasn’t so much a sacrifice as it was a way to have it all. I decided that no matter what job I held, I was working toward the future I wanted.

So I worked. And worked some more. Then took a break to enjoy some employee-discounted caffeine, and went right back to work. Did I sometimes feel like I was missing out? Yep. Did both jobs warrant more of my time than I had to give? Of course. But I wouldn’t trade anything for the independence and opportunity that a full-time job paired with a part-time job gave me: to live my life the way I wanted and to chase my dreams. Does this life of sacrifice sound like something you’re interested in? Good. That means you’re not afraid of a little hard work, and a couple of sleepless months or years, to get you where you want to be.

The following are some tips to keep in mind when searching for the perfect part-time career to combine with your already jam-packed schedule:


1. Flexibility
This is non-negotiable... kind of like your full-time job. You need to look for a job that understands what your current time commitment is, and is willing to work around it. Maybe this means working nights or weekends, or freelancing so you can create your own schedule. Whatever you choose, you need to make sure both you and your boss both understand where your priorities are.

2. Benefits
No, I'm not talking about a 401k here. Choose something that supplements your full-time job and benefits more than just your bank account. For me, my barista career had two big benefits. First - free drinks! Matcha lattes add up, guys, and this was a pretty great way to supplement my need for them (and learn to make things like the pros in the process!) Second - new people. I was new to the city when I started my job as a barista, and I couldn’t have found a better way to meet people - both co-workers and customers - from all walks of life. Whether you're using your job to master your craft or to abuse an employee discount, just make sure it's working for you as much as you are working for it. You might even find yourself killing two birds with one stone in the process.

3. Passion
It’s a widely known fact that working a second job is exhausting. Period. Whether it's rolling out of bed to work early on the weekend, or rushing from one job to the other late at night, there's always going to be moments where you ask yourself if it’s really worth it. Pro tip: make it worth it. Choose something you enjoy doing, and something you’re (even mildly) passionate about! It doesn't have to fuel your career growth – but it needs to fuel your soul. For me, I love tea! So learning about the rituals, processes and tasting notes was really exciting to me. Plus, it prepared me for all the wine tasting I'd be doing when I'd run away to Napa.


I waited three years before I left my part-time job. Three years! Or, by my math, 150 weekends - give or take. That might seem like a lot, but it was what I needed. Could I have left my full-time job for a more well paying job in another industry? Certainly. I have the recruiter emails to prove it. But that other job would have probably required more time, and for me, it all came down to priorities. This was the city I wanted, the career I had dreamed of, and the life I was meant to live. So what if it meant sacrificing sleep? For me it was more than worth it.

How did I get where I am today? Why, with a little bit of caffeine and a whole lot of hard work.



Mandy spends her days working in public relations, specializing in sustainability and corporate responsibility - a job which not only fuels her soul but also pays her San Francisco rent. She spends her (virtually nonexistent) free time exploring the Bay Area craft beer scene, working on her rock collection and wishing her cat would be the big spoon sometimes. For additional sass and details of her life held together by caffeine and dry shampoo, follow her on twitter @WayToRepresent.

BABE #87: KAT MAISANO,<br>Owner @ Keep Going Kat

BABE #87: KAT MAISANO,
Owner @ Keep Going Kat

BABE #86: RION PAIGE, Singer + Staff Songwriter @ Floor Six Publishing BMI

BABE #86: RION PAIGE, Singer + Staff Songwriter @ Floor Six Publishing BMI